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Development of Self-Assembled Supramolecular Catalysts and Their Applications to Organic Synthesis


Correspondenceauthor, e-mail: shi-ike @ pharm. teikyo-u. tic. Jp714 Fudan University ( Natural Science) Vol.44 effectsusinglbonoxidationofalcoholswereexamined (Scheme2) [] la (x = O05) 1b (x = O) Scheme1DesignofthermomorphicpolymersupportedPWl2O40 a complex (1) 2aPO90C6h '(). 1stuse: 92%: 2nduse: 92%: 3rduse: 90% Scheme2Oxidationof1-phenyl -1 a propanolbyrecycledlb (3) AnassembledinsolublecatalystPdAS 【 . JandPdAS-V 【 preparedfrompalladium ((NH4) 2PdCh) andnon-cross-linkedamphiphiliccopolymer (poly (N-isopropylacryl-amide-co -4 a diphenylstyrylphosphine)) wasdeveloped. ItWasfoundthatPdASandPdAS-VareexcellentcatalystsfortheSuzuki-MiyauraandMi-sorogi-Heckreactionsonthreepoints: 1) Theuseof8X10-5X10-4molequivofthecatalystsaffordedthecouplingproductsefficientlywiththeextremelyhighturnovernumber (TON), 2) ThecatalystsWasreusableinmanyrepeatedtimeswithoutlossofcatalyticactivity, 3) Thecatalystsshowedgoodstabilityinanyreactionmedia (i.e., water, aqueousoranhydrousorganicsolvents). Theseexcellentapplicationstoorganicsynthesiswillbepresented. Referell ~ es: [1] a) YamadaYMA, IchinoheM, TakahashiH, ela1. OrgLelt, 2001,3:1837.1841; b) YamadaYMA,[link widoczny dla zalogowanych], TabataH, Takahasl ~ H, eta1. Synlelt ,2002:2031-2034; C) YamadaYMA, TabataH, IchinoheM, ela1. rahedron, 2004,6 O: 4087.4096. [2] Hamam0toH, SuzukiY, YamadaYMA, eta1. AngewCAernIntnlEd, 2005,44:4536.4538. [3] a) YamadaYMA, Ta1'edaK, TakahashiH, ela /. OrgLet ,2002,4:3371-3374; b) YamadaYMA, Ta1'e. daK, TakahashiH, eta1. JOrgChern, 2003,68:7733.7741. [4] a) YamadaYMA, TakedaK, TakahashiH, eta1. retraJ ~ edronLelt, 2003,44:2379.2382; b) YamadaYMA, TakedaK, TakahashiH, ela1. Yetrahedron, 2004,60:4097.4105.